Category: 919103-45-0

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 919103-45-0, name is 6-Iodoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

Step 4: N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), 6-iodooxindole (as prepared in Preparation 1; 0.5 g, 1.93 mmol) and N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-mercapto-benzamide (as prepared in step 3 above; 0.477 g, 1.93 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). Isopropanol (3.0 mL) and ethylene glycol (0.250 mL) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80 C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (20 mL) and water (10 mL). The mixture was acidified with 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with EtOAc (2×20 mL). The organic layers were combined, dried over silica gel, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant 10 to 40% EtOAc in Hexanes) affording the title compound as a pale yellow solid (0.379 g, 1.01 mmol, 52% yield).

Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 919103-45-0.

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 919103-45-0, name is 6-Iodoindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 919103-45-0, Recommanded Product: 919103-45-0

0.88 g (7.23 mmol) 4-/V,/V-dimethylaminopyridine and 44.6 mL (101 .2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) 6-iodo-1 ,3-dihydro-indol-2- one in 125.0 mL /V,/V-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10C to the reaction mixture and stirred for 2 h at -10C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL cone, hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50C in vacuo. [M+H]+: 364

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ZAHN, Stephan Karl; BISTER, Bojan; SINI, Patrizia; WO2014/9319; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 919103-45-0, name is 6-Iodoindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Iodoindolin-2-one

Step 4: N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), 6-iodooxindole (as prepared in Preparation 1; 0.5 g, 1.93 mmol) and N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-mercapto-benzamide (as prepared in step 3 above; 0.477 g, 1.93 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). Isopropanol (3.0 mL) and ethylene glycol (0.250 mL) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80 C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (20 mL) and water (10 mL). The mixture was acidified with 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with EtOAc (2×20 mL). The organic layers were combined, dried over silica gel, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant 10 to 40% EtOAc in Hexanes) affording the title compound as a pale yellow solid (0.379 g, 1.01 mmol, 52% yield).

The synthetic route of 919103-45-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 919103-45-0, name is 6-Iodoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

0.88 g (7.23 mmol) 4-N,N-dimethylaminopyridine and 44.6 mL (101.2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) 6-iodo-1,3-dihydro-indol-2-one in 125.0 mL N,N-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10 C. to the reaction mixture and stirred for 2 h at -10 C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL conc. hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50 C. in vacuo.

The synthetic route of 919103-45-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ZAHN, Stephan Karl; SINI, Patrizia; BISTER, Bojan; US2014/18405; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 919103-45-0, name is 6-Iodoindolin-2-one, molecular formula is C8H6INO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C8H6INO

[0496] A nitrogen purged vessel is loaded with starting material 6-Iodoindolinone (105 kg, 405 mol, 1.0 eq), catalyst 4-dimethylaminopyridine (DMAP) (2.52 kg) under argon counter flow. Then triethylamine (145 kg, 3.5 eq) and solvent 2-methyltetrahydrofuran (605 kg) are charged to the vessel and the resulting solution is cooled to -15 C. to -5 C. (preferentially -10 C.). Benzoylchloride (176.6 kg, 3.1 eq) is added to this mixture at an internal temperature of -10 C. to 50 C. within at least 30 min. [0497] The addition funnel is then flushed with 2-methyltetrahydrofuran (22 kg) and the reaction mixture is stirred for an additional hour at an internal temperature of 10 to 30 C. If the content of starting material 6-iodoindolinone is greater than 2.5 area % (HPLC), another portion of benzoylchloride (5.7 kg) is added to complete the reaction. If the content of starting material 6-iodoindolinone is smaller than 2.5 area % (HPLC), lithium hydroxide (59.4 kg, 6.0 eq) is added in 5 differently sized portions (1st: 18.0 kg, 2nd: 6.0 kg, 3rd: 6.0 kg, 4th: 15.0 kg, 5th: 14.4 kg) in a temperature controlled manner: After the two first portions, the mixture is stirred for 1 hour. After portion 3 and 4, the mixture is stirred for 30 min. After the last portion, the mixture is stirred for two hours. The reaction mixture (suspension) is then stirred for at least 12 hours at an internal temperature of 20 to 30 C. If the content of the non isolated intermediate of formula (V) is smaller than 0.5 area % (HPLC), water (525 L) is added and the mixture is heated to an internal temperature of 60 to 70 C. under stirring. Then the stirrer is switched off, the mixture is settled down and the phases are separated at an internal temperature of 60 to 70 C. To the upper organic layer, water (525 L) is added and a second phase separation is carried out at an internal temperature of 60 to 70 C. (Optionally, the mixture might be left stand at room temperature for up to 24 hours.) Then a partial solvent switch to tetrahydrofuran is carried out: Solvent is distilled off three times at a jacket temperature of 70 C. down to a residual volume of 390 L followed by addition of tetrahydrofuran (1st: 233 kg, 2nd: 233 kg, 3rd: 117 kg). For crystallization, firstly, methanol (83 kg) is added. [0498] Optionally, the mixture might be left stand at room temperature for up to 24 hours. Secondly, water (112 L) is added at an internal temperature of 60 to 70 C., followed by addition of conc. hydrochloric acid (156.2 kg). The addition funnel is flushed with water (20 L). The resulting suspension is cooled to 20 to 30 C. within at least 70 min (optionally, the mixture might be left stand at room temperature for up to 72 hours) and then to an internal temperature of minus 5 to 5 C. within at least 30 min. The suspension is then centrifuged and the solid is washed with water (368 L) followed by methanol (112 kg) and dried at a jacket temperature of 50 C. until <=1% of residual solvent is reached. The enol product of formula (IV) is obtained as solid in 84.6% yield. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 919103-45-0, its application will become more common. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MAIER, Gerd-Michael; BAUM, Anke; BETZEMEIER, Bodo; HENRY, Manuel; HERTER, Rolf; REISER, Ulrich; SINI, Patrizia; WEBER, Dirk; WERTHMANN, Ulrike; ZAHN, Stephan Karl; US2014/18372; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 919103-45-0,Some common heterocyclic compound, 919103-45-0, name is 6-Iodoindolin-2-one, molecular formula is C8H6INO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A nitrogen purged vessel is loaded with starting material 6-lodoindolinone (1 05kg,405mo1, 1,0 eq), catalyst 4-dimethylaminopyridine (DMAP) (2,52 kg) under argoncounter flow. Then triethylamine (145 kg, 3,5 eq) and solvent 2-methyltetrahydrofuran(605 kg) are charged to the vessel and the resulting solution is cooled to -15 00 to-S00 (preferentially -10C). Benzoylchloride (176,6 kg, 3,1 eq) is added to this mixture atan internal temperature of 100C to 50C within at least 30mm.The addition funnel is then flushed with 2-methyltetrahydrofuran (22 kg) and the reaction mixture is stirred for an additional hour at an internal temperature of 10 to 30C. If the content of starting material 6-iodoindolinone is greater than 2,5 area%(H PLC), another portion of benzoylchloride (5,7 kg) is added to complete the reaction. If the content of starting material 6-iodoindolinone is smaller than 2,5 area% (H PLC), lithium hydroxide (59,4 kg, 6,0 eq) is added in 5 differently sized portions (1st: 18,0 kg, 2?: 6,0 kg, 3: 6,0 kg, 41h: 15,0 kg, 5th: 14,4 kg) in a temperature controlled manner:After the two first portions, the mixture is stirred for 1 hour. After portion 3 and 4, the mixture is stirred for 30mm. After the last portion, the mixture is stirred for two hours. The reaction mixture (suspension) is then stirred for at least 12 hours at an internal temperature of 20 to 30 C. If the content of the non isolated intermediate of formula (V) is smaller than 0,5 area% (H PLC), water (525 L) is added and the mixture is heatedto an internal temperature of 60 to 7000 under stirring. Then the stirrer is switched off, the mixture is settled down and the phases are separated at an internal temperature of 60 to 70C. To the upper organic layer, water (525 L) is added and a second phase separation is carried out at an internal temperature of 60 to 70C. (Optionally, the mixture might be left stand at room temperature for up to 24 hours.) Then a partial solvent switch to tetrahydrofuran is carried out: Solvent is distilled off three times at a jacket temperature of 70C down to a residual volume of 390L followed by addition of tetrahydrofuran (1st: 233 kg, 2nd. 233 kg, 3rd. 117 kg). For crystallization, firstly, methanol (83 kg) is added.Optionally, the mixture might be left stand at room temperature for up to 24 hours. Secondly, water (112 L) is added at an internal temperature of 60 to 70C, followed by addition of conc. hydrochloric acid (156,2 kg). The addition funnel is flushed with water (20 L). The resulting suspension is cooled to 20 to 30C within at least 70mm (optionally, the mixture might be left stand at room temperature for up to 72 hours) and then to an internal temperature of minus 5 to 5 C within at least 30mm. The suspension is then centrifuged and the solid is washed with water (368 L) followed by methanol (112 kg) and dried at a jacket temperature of 50C until <= 1% of residual solvent is reached. The enol product of formula (IV) is obtained as solid in 84,6% yield. The synthetic route of 919103-45-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MAIER, Gerd-Michael; BAUM, Anke; BETZEMEIER, Bodo; HENRY, Manuel; HERTER, Rolf; REISER, Ulrich; SINI, Patrizia; WEBER, Dirk; WERTHMANN, Ulrike; ZAHN, Stephan Karl; WO2014/9318; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 919103-45-0 as follows. Application In Synthesis of 6-Iodoindolin-2-one

Preparation 2: (2-Oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzoic acid CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), 6-iodooxindole (as prepared in Preparation 1; 1.0 g, 4.0 mmol) and 2-mercapto-benzoic acid (0.62 g, 4.0 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). 2-Propanol (5.0 mL) and ethylene glycol (0.5 mL, 8.0 mmol) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80 C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (10 mL) and water (10 mL). The mixture was acidified of to a pH=3-4 with the addition of 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with additional EtOAc (10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant starting with 5% MeOH in CHCl3 increasing to 10% MeOH in CHCl3) affording the title compound as a pale yellow solid (0.228 g, 0.77 mmol, 20% yield).

According to the analysis of related databases, 919103-45-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem